Sitter Stories

2,111 results
Orientation
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The Baby-Sitter Diaries

by OregonDavid on Sep 12, 2017
First Time

I started having a fetish for the baby-sitter when she was young, much younger than her current age of twenty-three years. She has been the only baby-sitter of my three boys for the last eight years. Her mother is a colleague and her father is my best friend. She currently attends the college where I have taught for the last twenty two years, and I have lite...

The God-Fearing Sitter

by Eden_Apple on Aug 18, 2017
First Time

Kelly sat atop her bed with her knees held tight to her chest staring out the window of her 2nd story bedroom. Although she lived in a beautifully over-stated home on what the less fortunate would call the "rich" side of town she felt she may as well be sitting in a dollhouse where she would be just as confined and surrounded by obnoxious pink furniture. Her...

Not That Complicated/Cheater

by sexileo21 on Sep 3, 2017
Erotic Couplings

Here I have the first part of two stories I want to work on. Now that Christmas break is near and I'll have a ton of free time, I want to get back into writing. Please vote on which story you would rather read in the comment section. Don't be shy to include what you think should happen as well. I would love to incorporate some of your ideas! If you like both...

The Prisoner Ch. 12

by EZ4BLKcock on Sep 16, 2017
Interracial Love

Over the next couple of months Christina became a regular fixture at my apartment. She was just as wild as I when it came to new sexual experiences. We included Bill in all our activities when he was in town. I finally left for maternity leave as scheduled. I went into labor a week early, Dan rushed me to the hospital. After fifteen hours of labor I gave bi...

Family is Not Blood Ch. 02

by wieliczka on Sep 15, 2017
Romance

After I had completely humiliated my cheating wife and her cheating mother in front of our families and friends, I needed to move on with life. The next two months were hectic for me. I had already updated my driver's license, new bank accounts, changed passwords on so many accounts and changed so many things that a divorced man would do. Still, I was not...

The Homewrecker Ch. 07

by Rimcrim on May 7, 2018
Fetish

After what seemed like an endless cycle of soaping up Fabonita's ass crack, washing it, and drying it, she finally deemed it clean enough. I waited on her to get up, and walked behind her like a scolded puppy. "Apologize for the delay, Michael," she demanded. "Making dear Carol wait so long that the food must have gotten cold." Carol was shocked and a litt...

Color Coordination

by EriAliSaa on Sep 14, 2017
Exhibitionist & Voyeur

I woke this morning a little late crawled out of bed, looked down on my sleeping baby in the crib next to my bed and threw on one of my hubby's NFL replica jerseys. The mornings have finally had a chill about them after a long 23 straight days with above 90 degree heat. It felt divine, cool air seeping through the holes in the jersey, and on my bare skin und...

Playtime with Anna

by ChaseQ on Sep 16, 2017
Anal

My wife Anna and I enjoy a fairly wild sex life. We have been married for almost ten years and the sex has continued to be exciting. She knows what turns me on and thrives on it. I know that every so often she is going to surprise me with some sexual play that is out of the ordinary from what I hear other guys talk about with their women. Just about every o...

A Rainy Night Alone Ch. 02

by cashfan47 on Sep 16, 2017
Romance

Carla is sitting on a park bench in Garfield Park, watching her two year old twins, Emily and Amber, playing in the sandbox when she sees Toby walking towards her pushing a stroller. She inhales sharply at seeing him as she remembers the last time they were together and the major fight they had. She notices the stroller and wonders why he is pushing it. Tob...

We Went Out Saturday Night

by TX-Carl on Sep 19, 2017
Erotic Couplings

I took my wife out for a date on Saturday night, and it was good. I told her she had to wear her black leather skirt, black spandex top with short sleeves and no bra or panties. She said she would if I would not wear my boxers. I said ok, let's go! She wore some open heeled shoes and had red nail polish and lip stick on. She looked good! I got a sitter and...